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Meet Our Ex-Boyfriends (We Love Them All, Really)

Breakups suck. But on the bright side, that’s how we often end up with that one really great piece of clothing, the one we “borrowed” enough to eventually own. One such trophy—the lovingly worn-in button-down shirt with a relaxed fit—plays a big part in our wardrobes, so we created a whole group of ’em called, fittingly, the Ex-Boyfriends. They come in a variety of shapes and, like all good past relationships, they’re all a little bit different. Here, our designer Ash introduces you to three of them, and explains why these relationships might just last.

Classic Ex-Boyfriend Shirt

To help compare each shirt, Ash explained the elements of the traditional fit: slim cut, fitted in the shoulders and hitting below your zipper. Our take on classic is a little roomier but definitely not boxy. “You can tuck it into jeans, add heels and look instantly pulled together,” Ash says. This fall, he wanted the fabric to match the timelessness of the shape and chose a supersoft flannel that feels like you’ve had it and loved it for years. “We call it the hand test. The softer it is to the touch, the better.”

It’s as if our classic button-down took a big deep breath. The entire shape is roomier, more relaxed and wider through the sleeves. “Oversized proportions feel modern, and they create a cool shape. For example, the back is longer and curved, so it looks great untucked,” says Ash. As for the pattern, he gave the classic polka dot an equally laid-back refresh. The little clusters of varying size look like they could’ve been applied by an artful hand. (And since he designed the pattern, they actually were.) “We really love a good dot,” says Ash, “Especially when paired with corduroys.”

Ash cut a narrower version of the standard button-down and called it “shrunken” around the office, and it stuck. So that’s what we called it. Meet the Shrunken Ex-Boyfriend, which is not only leaner but also hits at your hips.